Abstract
A series of (R)-2-amino-3-((aroylcarbamothioyl)thio)propanoic acid derivatives have been synthesised by a one-pot, three-component reaction of L-cysteine with ammonium thiocyanate in the presence of various acid chlorides under solvent-free conditions in excellent yields. These compounds were converted to (R)-2-thioxothiazolidine-4-carboxylic acid in water under reflux conditions.
References
1.
Droge W.
,
Hack V.
,
Breitkreutz R.
,
Holm E.
,
Shubinsky G.
,
Schmid E.
, and
Galter D.
, BioFactors , 1998 , 8 , 97 .
2.
Osman L.P.
,
Mitchell S.C.
, and
Waring R.H.
, Sulfur Rep. , 1997 , 20 , 155 .
3.
Santhiago M.
, and
Vieira I.C.
, Sens. Actuators B , 2007 , 128 , 279 .
4.
Guo Z.
,
Smith T.J.
,
Wang E.
,
Sadrieh N.
,
Ma Q.
,
Thomas P.E.
, and
Yang C.S.
, Carcinogenesis , 1992 , 13 , 2205 .
5.
Sparnins V.L.
,
Venegas P.L.
, and
Wattenberg L.W.
, J. Natl. Cancer Inst. , 1982 , 68 , 493 .
6.
Zhang Y.
, and
Talalay P.
, Cancer Res. , 1998 , 58 , 4632 .
7.
Hecht S.S.
, Drug Metabolism Rev. , 2000 , 32 , 395 .
8.
Sharma S.
, Sulfur Rep. , 1989 , 8 , 327
9.
Drobnica L.
,
Kristian P.
, and
Augustin J.
, The chemistry of cyanates and their thio derivatives;
Patai S.
, ed. Wiley : Chichester, UK , 1977 ; pp. 1003 .
10.
Mennicke W.H.
,
Görler K.
, and
Krumbiegel G.
, Xenobiotica , 1983 , 13 , 203 .
11.
Ioannou Y.M.
,
Burka L.T.
, and
Matthews H.B.
, Toxicol. Appl. Pharmacol. , 1984 , 75 , 173 .
12.
Eklind K.I.
,
Morse M.A.
, and
Chung F.L.
, Carcinogenesis , 1990 , 11 , 2033 .
13.
Jiao D.
,
Conaway C.C.
,
Wang M.H.
,
Yang C.S.
,
Koehl W.
, and
Chung F.L.
, Chem. Res. Toxicol. , 1996 , 9 , 932 .
14.
Kassahun K.
,
Davis M.
,
Hu P.
,
Martin B.
, and
Baillie T.
, Chem. Res. Toxicol. , 1997 , 10 , 1228 .
15.
Vermeulen M.
,
Van Rooijen H.J.M.
, and
Vaes W.H.J.
, J. Agric. Food Chem. , 2003 , 51 , 3554 .
16.
Yoneda K.
,
Ota A.
, and
Kawashima Y.
, Chem. Pharm. Bull. , 1993 , 41 , 876 .
17.
Matsui N.
,
Kajita S.
, and
Nakakawa H.
, JP 1095784 , 1998 [Chem. Abstr. , 1998 , 129 , 4647w ].
18.
Takashi J.
,
Nakaya M.
,
Inami S.
, and
Matsuno H.
, JP 09124647 , 1997 [Chem. Abstr. , 1997 , 127 , 65758p ].
19.
Reece J.E.
, and
Fozzard G.B.
, US 3697516 , 1972 [Chem. Abstr. , 1972 , 78 , 16203 ].
20.
Nakaya M.
,
Ebihara K.
,
Matsuno H.
,
Shiraishi S.
,
Oonuma K.
, and
Yamada H.
, JP 06312985 , 1994 [Chem. Abstr. , 1995 , 122 , 187572r ].
21.
Greenwald R.B.
,
Pendri A.
,
Martinez A.
,
Gilbert C.
, and
Bradley P.
, Bioconjugate Chem. , 1996 , 7 , 638 .
22.
Sweetman B.J.
,
Vestling M.M.
,
Ticaric S.T.
,
Kelly P.L.
, and
Field L.
, J. Med. Chem. , 1971 , 14 , 868 .
23.
Mohebat R.
, and
Mohammadian G.
, J. Chem. Res. , 2012 , 36 , 626 .
24.
Mohebat R.
,
Mosslemin M.H.
,
Dehghan-Darehshiri A.
, and
Hassanabadi A.
, J. Sulfur Chem. , 2011 , 32 , 557 .
25.
Mohebat R.
, and
Saeedi F.
, J. Sulfur Chem. , 2012 , 33 , 583 .
26.
Zweifel T.
,
Naubron J.-V.
, and
Gruetzmacher H.
, Angew. Chem., Int. Ed. , 2009 , 48 , 559 .
27.
Ramon R.S.
,
Marion N.
, and
Nolan S.P.
, Chem. Eur. J. , 2009 , 15 , 8695 .
28.
Pouchert C.J.
, The Aldrich Library of NMR Spectra , 2nd edn. Aldrich Chemical Company, Inc. Milwaukee , 1983 , Vols 1 and 2 .
29.
Furniss B.S.
,
Hannaford A.J.
,
Smith P.W.G.
, and
Tatchell A.R.
, Vogel's textbook of practical organic chemistry , 5th edn. Longman , Harlow , 1989 .
30.
Huang H.
,
Li Y.
,
Hu X.
,
Tian Q.
,
Lang M.
,
Li W.
, and
Wang Y.
, Chin. J. Org. Chem. , 1995 , 15 , 67 .
31.
Li Y.-Z.
,
Guo C.-X.
,
Hu X.-S.
, and
Huang H.-M.
, Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/Chem. J. Chin. Universities , 1997 , 18 , x17 .
32.
Dobson A.J.
, and
Gerkin R.E.
, Acta Crystallogr. , 1998 , c54 , 1634 .